The Last International Playboy (2008)

The ultimate New York City playboy Jack Frost (Jason Behr) is shattered when he
discovers his one true love Carolina (Monet Mazur) is about to marry another man. Still haunted by his mother's suicide, Jack spirals into a
self-destructive cycle of whiskey and reckless behaviour, while his best friends Ozzy (Krysten Ritter) and Scotch (Mike Landry) try to jar
him back to reality. Strangely enough, it's Jack's eleven year-old neighbour, Sophie (India Ennenga), who helps the drowning urbanite shake
off the nostalgia and excess that threaten to consume him.

Jack's Apartment, 227 Centre Street and Grand Street, Manhattan.

This building was in fact the previous headquarters for New York Police department.